ES2244082T3 - Derivados de sulfonamida que son antagonistas del receptor 5-ht6 y procedimiento para su preparacion. - Google Patents
Derivados de sulfonamida que son antagonistas del receptor 5-ht6 y procedimiento para su preparacion.Info
- Publication number
- ES2244082T3 ES2244082T3 ES98945162T ES98945162T ES2244082T3 ES 2244082 T3 ES2244082 T3 ES 2244082T3 ES 98945162 T ES98945162 T ES 98945162T ES 98945162 T ES98945162 T ES 98945162T ES 2244082 T3 ES2244082 T3 ES 2244082T3
- Authority
- ES
- Spain
- Prior art keywords
- methoxy
- methylpiperazin
- piperazin
- benzenesulfonamide
- ylbenzenesulfonamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229940124530 sulfonamide Drugs 0.000 title claims description 8
- 150000003456 sulfonamides Chemical class 0.000 title description 6
- 239000005557 antagonist Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 238000011282 treatment Methods 0.000 claims abstract description 15
- -1 2-Trifluoromethoxyphenyl Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- POLGADUNOHECAM-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-7-(trifluoromethyl)-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(=CC=C3CCC2)C(F)(F)F)C=C1N1CCN(C)CC1 POLGADUNOHECAM-UHFFFAOYSA-N 0.000 claims description 4
- CFWBBEJEOVLFTP-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(2-propan-2-ylphenyl)benzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C(C)C)C=C1N1CCNCC1 CFWBBEJEOVLFTP-UHFFFAOYSA-N 0.000 claims description 4
- PCLYDRYQTVZJKG-UHFFFAOYSA-N 5,8-dimethoxy-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound C1CC=2C(OC)=CC=C(OC)C=2CN1S(=O)(=O)C(C=1)=CC=C(OC)C=1N1CCN(C)CC1 PCLYDRYQTVZJKG-UHFFFAOYSA-N 0.000 claims description 4
- RDYTVZIDIIJAPA-UHFFFAOYSA-N 5-chloro-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1,3-dihydroisoindole;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)N2CC3=CC(Cl)=CC=C3C2)C=C1N1CCN(C)CC1 RDYTVZIDIIJAPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- FLZVBXAXKHVZDG-UHFFFAOYSA-N n-(3-bromophenyl)-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Br)C=CC=2)C=C1N1CCN(C)CC1 FLZVBXAXKHVZDG-UHFFFAOYSA-N 0.000 claims description 4
- MOVUYASQFVYATN-UHFFFAOYSA-N n-(3-bromophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Br)C=CC=2)C=C1N1CCNCC1 MOVUYASQFVYATN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IWRPWICOPHVPPS-UHFFFAOYSA-N 5,8-dichloro-2-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)N2CC3=C(Cl)C=CC(Cl)=C3CC2)C=C1N1CCNCC1 IWRPWICOPHVPPS-UHFFFAOYSA-N 0.000 claims description 3
- OKZVHBPLHUKXDO-UHFFFAOYSA-N 5,8-dimethoxy-2-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC=2C(OC)=CC=C(OC)C=2CN1S(=O)(=O)C(C=1)=CC=C(OC)C=1N1CCNCC1 OKZVHBPLHUKXDO-UHFFFAOYSA-N 0.000 claims description 3
- FZGRQZBGYFJAIV-UHFFFAOYSA-N 6-chloro-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-5-methyl-2,3-dihydroindole;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)N2C3=CC(Cl)=C(C)C=C3CC2)C=C1N1CCNCC1 FZGRQZBGYFJAIV-UHFFFAOYSA-N 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- XLCOBLJQIQRIOW-UHFFFAOYSA-N 1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-5-methyl-6-(trifluoromethyl)-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(=C(C)C=C3CC2)C(F)(F)F)C=C1N1CCNCC1 XLCOBLJQIQRIOW-UHFFFAOYSA-N 0.000 claims description 2
- UDOCGLOTHDGSLO-UHFFFAOYSA-N 1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-7-(trifluoromethyl)-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(=CC=C3CCC2)C(F)(F)F)C=C1N1CCNCC1 UDOCGLOTHDGSLO-UHFFFAOYSA-N 0.000 claims description 2
- CKNDHUOEHNPHQM-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=CC=C3CCC2)C=C1N1CCN(C)CC1 CKNDHUOEHNPHQM-UHFFFAOYSA-N 0.000 claims description 2
- NHXUMECGHRXJTA-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-5-(trifluoromethyl)-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(C=C3CC2)C(F)(F)F)C=C1N1CCN(C)CC1 NHXUMECGHRXJTA-UHFFFAOYSA-N 0.000 claims description 2
- DAEYTCREGCXPTF-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-6-(trifluoromethyl)-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(=CC=C3CC2)C(F)(F)F)C=C1N1CCN(C)CC1 DAEYTCREGCXPTF-UHFFFAOYSA-N 0.000 claims description 2
- VYPPBIQIZMFWGO-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-6-methyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(C)C=C3CCC2)C=C1N1CCN(C)CC1 VYPPBIQIZMFWGO-UHFFFAOYSA-N 0.000 claims description 2
- BMWCFEKILGGNEW-UHFFFAOYSA-N 2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-5-pyridin-3-yl-2,3-dihydro-1h-indole Chemical compound COC1=CC=C(S(=O)(=O)C2NC3=CC=C(C=C3C2)C=2C=NC=CC=2)C=C1N1CCN(C)CC1 BMWCFEKILGGNEW-UHFFFAOYSA-N 0.000 claims description 2
- KNJIUHVHONVBLD-UHFFFAOYSA-N 2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-6-pyridin-3-yl-2,3-dihydro-1h-indole Chemical compound COC1=CC=C(S(=O)(=O)C2NC3=CC(=CC=C3C2)C=2C=NC=CC=2)C=C1N1CCN(C)CC1 KNJIUHVHONVBLD-UHFFFAOYSA-N 0.000 claims description 2
- YTQCQZLEPSVMDU-UHFFFAOYSA-N 2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-7-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC=CC=2)C=C1N1CCN(C)CC1 YTQCQZLEPSVMDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- FLBDNSQBPJFQAV-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-(2-methylsulfanylphenyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)SC)C=C1N1CCN(C)CC1 FLBDNSQBPJFQAV-UHFFFAOYSA-N 0.000 claims description 2
- XZHQQZBHLGUOSJ-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-(2-pyrrol-1-ylphenyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)N2C=CC=C2)C=C1N1CCN(C)CC1 XZHQQZBHLGUOSJ-UHFFFAOYSA-N 0.000 claims description 2
- MEKZLHDZQUCNLX-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-(4-pentoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OCCCCC)=CC=C1NS(=O)(=O)C1=CC=C(OC)C(N2CCN(C)CC2)=C1 MEKZLHDZQUCNLX-UHFFFAOYSA-N 0.000 claims description 2
- UVDJVPHZRKZUCS-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-(5,6,7,8-tetrahydronaphthalen-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=3CCCCC=3C=CC=2)C=C1N1CCN(C)CC1 UVDJVPHZRKZUCS-UHFFFAOYSA-N 0.000 claims description 2
- LTYKRQJQCUCMDA-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-[3-(1,3-oxazol-5-yl)phenyl]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(C=CC=2)C=2OC=NC=2)C=C1N1CCN(C)CC1 LTYKRQJQCUCMDA-UHFFFAOYSA-N 0.000 claims description 2
- JKZBOPQIKSVXRR-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-[4-(4-nitrophenyl)sulfanylphenyl]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=CC(SC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)C=C1N1CCN(C)CC1 JKZBOPQIKSVXRR-UHFFFAOYSA-N 0.000 claims description 2
- ZFRNCAMEAUGFPK-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-naphthalen-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C3=CC=CC=C3C=CC=2)C=C1N1CCN(C)CC1 ZFRNCAMEAUGFPK-UHFFFAOYSA-N 0.000 claims description 2
- JFOODCMHJBJBFA-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(2,4,5-trichlorophenyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)Cl)C=C1N1CCNCC1 JFOODCMHJBJBFA-UHFFFAOYSA-N 0.000 claims description 2
- GBLPUEUGKDWWSS-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(2-prop-1-en-2-ylphenyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C(C)=C)C=C1N1CCNCC1 GBLPUEUGKDWWSS-UHFFFAOYSA-N 0.000 claims description 2
- PSJNZSRNDWLNBK-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(2-propylphenyl)benzenesulfonamide Chemical compound CCCC1=CC=CC=C1NS(=O)(=O)C1=CC=C(OC)C(N2CCNCC2)=C1 PSJNZSRNDWLNBK-UHFFFAOYSA-N 0.000 claims description 2
- NYTMTUMDTVVQNA-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(4-propan-2-ylphenyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=CC(=CC=2)C(C)C)C=C1N1CCNCC1 NYTMTUMDTVVQNA-UHFFFAOYSA-N 0.000 claims description 2
- WHGJISFGBPKDCM-UHFFFAOYSA-N 4-methoxy-n-(2-methoxy-5-phenylphenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1NS(=O)(=O)C(C=1)=CC=C(OC)C=1N1CCNCC1 WHGJISFGBPKDCM-UHFFFAOYSA-N 0.000 claims description 2
- XLOSDXQNUBXRTL-UHFFFAOYSA-N 4-methoxy-n-(2-methoxy-6-methylphenyl)-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=CC(C)=C1NS(=O)(=O)C1=CC=C(OC)C(N2CCN(C)CC2)=C1 XLOSDXQNUBXRTL-UHFFFAOYSA-N 0.000 claims description 2
- IWMCIQGBNDFJKU-UHFFFAOYSA-N 4-methoxy-n-(2-methoxydibenzofuran-3-yl)-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=3C4=CC=CC=C4OC=3C=2)OC)C=C1N1CCN(C)CC1 IWMCIQGBNDFJKU-UHFFFAOYSA-N 0.000 claims description 2
- FVGSGZBVVBKGCH-UHFFFAOYSA-N 4-methoxy-n-(2-methyl-5-nitrophenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=C(C=2)[N+]([O-])=O)C)C=C1N1CCNCC1 FVGSGZBVVBKGCH-UHFFFAOYSA-N 0.000 claims description 2
- GTKBYXRGPIGSOV-UHFFFAOYSA-N 4-methoxy-n-(2-methylphenyl)-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C)C=C1N1CCN(C)CC1 GTKBYXRGPIGSOV-UHFFFAOYSA-N 0.000 claims description 2
- QVVYNLXLIIGBPZ-UHFFFAOYSA-N 4-methoxy-n-(2-methylphenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C)C=C1N1CCNCC1 QVVYNLXLIIGBPZ-UHFFFAOYSA-N 0.000 claims description 2
- ILRRXOFKVCSZET-UHFFFAOYSA-N 4-methoxy-n-(2-methylsulfanylphenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)SC)C=C1N1CCNCC1 ILRRXOFKVCSZET-UHFFFAOYSA-N 0.000 claims description 2
- QJEBJIGMNFTICZ-UHFFFAOYSA-N 4-methoxy-n-(2-phenylphenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1N1CCNCC1 QJEBJIGMNFTICZ-UHFFFAOYSA-N 0.000 claims description 2
- IVTKBMDVXZBDSV-UHFFFAOYSA-N 4-methoxy-n-(3-methylphenyl)-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(C)C=CC=2)C=C1N1CCN(C)CC1 IVTKBMDVXZBDSV-UHFFFAOYSA-N 0.000 claims description 2
- WLYHCTGNUSMWKW-UHFFFAOYSA-N 4-methoxy-n-naphthalen-1-yl-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C3=CC=CC=C3C=CC=2)C=C1N1CCNCC1 WLYHCTGNUSMWKW-UHFFFAOYSA-N 0.000 claims description 2
- BMMOIADDFZZTNK-UHFFFAOYSA-N 5,6-dichloro-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=C(C(=C(Cl)C=C3)Cl)CC2)C=C1N1CCN(C)CC1 BMMOIADDFZZTNK-UHFFFAOYSA-N 0.000 claims description 2
- BPIIEZVZIXRCMW-UHFFFAOYSA-N 5,7-dichloro-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(Cl)=CC(Cl)=C3CCC2)C=C1N1CCNCC1 BPIIEZVZIXRCMW-UHFFFAOYSA-N 0.000 claims description 2
- ZOPSUSIHJUKCEA-UHFFFAOYSA-N 5,7-dichloro-1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(Cl)=CC(Cl)=C3CCC2)C=C1N1CCN(C)CC1 ZOPSUSIHJUKCEA-UHFFFAOYSA-N 0.000 claims description 2
- LWXPPFAQILVKSG-UHFFFAOYSA-N 5,8-dichloro-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=C(Cl)C=CC(Cl)=C3CC2)C=C1N1CCN(C)CC1 LWXPPFAQILVKSG-UHFFFAOYSA-N 0.000 claims description 2
- LELBOKCPTLNBDF-UHFFFAOYSA-N 5-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-6,7-dihydro-1h-pyrrolo[2,3-f]indole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=4C=CNC=4C=C3CC2)C=C1N1CCN(C)CC1 LELBOKCPTLNBDF-UHFFFAOYSA-N 0.000 claims description 2
- SCGVPHBYFIVKQH-UHFFFAOYSA-N 5-bromo-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=CC=CC(Br)=C3CC2)C=C1N1CCN(C)CC1 SCGVPHBYFIVKQH-UHFFFAOYSA-N 0.000 claims description 2
- ASMBQCAYRRHYLW-UHFFFAOYSA-N 5-iodo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(I)C=C3CC2)C=C1N1CCNCC1 ASMBQCAYRRHYLW-UHFFFAOYSA-N 0.000 claims description 2
- NZVNEMOVXUPIBS-UHFFFAOYSA-N 6,7,8-trimethoxy-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=C(OC)C(OC)=C(OC)C=C3CC2)C=C1N1CCN(C)CC1 NZVNEMOVXUPIBS-UHFFFAOYSA-N 0.000 claims description 2
- KYNVEGXEKYANKP-UHFFFAOYSA-N 6,7-dimethoxy-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=CC(OC)=C(OC)C=C3CC2)C=C1N1CCN(C)CC1 KYNVEGXEKYANKP-UHFFFAOYSA-N 0.000 claims description 2
- SDDYVBFUBSBDIV-UHFFFAOYSA-N 6-bromo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(Br)C=C3CCC2)C=C1N1CCNCC1 SDDYVBFUBSBDIV-UHFFFAOYSA-N 0.000 claims description 2
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- SKUZUMYFFXXCNO-UHFFFAOYSA-N 6-chloro-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=CC=C(Cl)C=C3CC2)C=C1N1CCN(C)CC1 SKUZUMYFFXXCNO-UHFFFAOYSA-N 0.000 claims description 2
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- ZMFKQRWTGQWRBC-UHFFFAOYSA-N 4-methoxy-3-(4-methylpiperazin-1-yl)-n-[2-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C(F)(F)F)C=C1N1CCN(C)CC1 ZMFKQRWTGQWRBC-UHFFFAOYSA-N 0.000 description 1
- GUZZHBFHDGKAPF-UHFFFAOYSA-N 5,7-dichloro-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-2h-quinoline;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)N2C3=CC(Cl)=CC(Cl)=C3CCC2)C=C1N1CCNCC1 GUZZHBFHDGKAPF-UHFFFAOYSA-N 0.000 description 1
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- ZAMJLADJGLXVOJ-UHFFFAOYSA-N 6-chloro-5-methyl-2,3-dihydro-1h-indole Chemical compound C1=C(Cl)C(C)=CC2=C1NCC2 ZAMJLADJGLXVOJ-UHFFFAOYSA-N 0.000 description 1
- XYBSZCUHOLWQQU-UHFFFAOYSA-N 7-bromoquinoline Chemical compound C1=CC=NC2=CC(Br)=CC=C21 XYBSZCUHOLWQQU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
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- 238000010367 cloning Methods 0.000 description 1
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- 239000012141 concentrate Substances 0.000 description 1
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- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
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- 239000004174 erythrosine Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
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- BMVXKXJFMOOBAX-UHFFFAOYSA-N n-(3-iodo-4-methylphenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)NC=2C=C(I)C(C)=CC=2)C=C1N1CCNCC1 BMVXKXJFMOOBAX-UHFFFAOYSA-N 0.000 description 1
- VCRIXXQTBUGMTA-UHFFFAOYSA-N n-(4-bromophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=CC(Br)=CC=2)C=C1N1CCNCC1 VCRIXXQTBUGMTA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/08—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9714530 | 1997-07-11 | ||
| GBGB9714530.4A GB9714530D0 (en) | 1997-07-11 | 1997-07-11 | Novel compounds |
| GB9724530 | 1997-11-19 | ||
| GBGB9724530.2A GB9724530D0 (en) | 1997-11-19 | 1997-11-19 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2244082T3 true ES2244082T3 (es) | 2005-12-01 |
Family
ID=26311860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98945162T Expired - Lifetime ES2244082T3 (es) | 1997-07-11 | 1998-07-09 | Derivados de sulfonamida que son antagonistas del receptor 5-ht6 y procedimiento para su preparacion. |
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| US (1) | US6316450B1 (de) |
| EP (1) | EP0994862B1 (de) |
| JP (1) | JP2002511097A (de) |
| KR (1) | KR20010021643A (de) |
| CN (1) | CN1087294C (de) |
| AR (1) | AR013199A1 (de) |
| AT (1) | ATE296811T1 (de) |
| AU (1) | AU736256B2 (de) |
| BR (1) | BR9810991A (de) |
| CA (1) | CA2296033A1 (de) |
| DE (1) | DE69830405T2 (de) |
| ES (1) | ES2244082T3 (de) |
| HU (1) | HUP0003073A3 (de) |
| IL (1) | IL133870A0 (de) |
| NO (1) | NO20000108L (de) |
| NZ (1) | NZ501258A (de) |
| PL (1) | PL338016A1 (de) |
| TR (1) | TR200000073T2 (de) |
| TW (1) | TW470743B (de) |
| WO (1) | WO1999002502A2 (de) |
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| US10821106B2 (en) | 2015-08-21 | 2020-11-03 | Srx Cardio, Llc | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate PCSK9 protein activity |
| WO2017147328A1 (en) | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| US10980806B2 (en) | 2016-03-24 | 2021-04-20 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer |
| CN111517963A (zh) * | 2020-06-02 | 2020-08-11 | 杭州福莱蒽特科技有限公司 | 环保型2,6-二氯-4-硝基苯胺的制备方法 |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2442851A1 (de) * | 1974-09-06 | 1976-03-18 | Hoechst Ag | Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung |
| US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
| DE69418045T2 (de) | 1993-08-06 | 1999-10-07 | Smithkline Beecham P.L.C., Brentford | Amidderivate als 5ht1d rezeptor antagonisten |
| FI935373A0 (fi) * | 1993-12-01 | 1993-12-01 | Iws International Inc | Kopplingsstycke eller koppling foer ledning |
| EP0733048A1 (de) * | 1993-12-07 | 1996-09-25 | Smithkline Beecham Plc | Heterocyclische biphenylylamide, verwendbar als 5ht1d antagonisten |
| GB9325827D0 (en) * | 1993-12-17 | 1994-02-23 | Smithkline Beecham Plc | Compounds |
| WO1997007120A1 (en) | 1995-08-11 | 1997-02-27 | Smithkline Beecham Plc | Biphenyl(thio)amide and biphenylethan(thi)one derivatives, their preparation and their use as 5-ht1d receptor antagonists |
| FR2740134B1 (fr) | 1995-10-18 | 1998-01-09 | Pf Medicament | Derives d'amines cycliques d'aryl-piperazines, leur preparation et les compositions pharmaceutiques les contenant |
| EP0883613A1 (de) * | 1996-02-09 | 1998-12-16 | Smithkline Beecham Plc | Sulfonamidederivate als 5ht7 rezeptor antagonist |
| US5939451A (en) * | 1996-06-28 | 1999-08-17 | Hoffmann-La Roche Inc. | Use of sulfonamides |
| DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| WO1998027058A2 (en) | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | N-piperazin-1-ylphenyl-benzamide derivatives |
-
1998
- 1998-07-09 EP EP98945162A patent/EP0994862B1/de not_active Expired - Lifetime
- 1998-07-09 PL PL98338016A patent/PL338016A1/xx unknown
- 1998-07-09 JP JP50818699A patent/JP2002511097A/ja not_active Ceased
- 1998-07-09 CN CN98806921A patent/CN1087294C/zh not_active Expired - Fee Related
- 1998-07-09 IL IL13387098A patent/IL133870A0/xx unknown
- 1998-07-09 TR TR2000/00073T patent/TR200000073T2/xx unknown
- 1998-07-09 NZ NZ501258A patent/NZ501258A/en unknown
- 1998-07-09 ES ES98945162T patent/ES2244082T3/es not_active Expired - Lifetime
- 1998-07-09 WO PCT/EP1998/004973 patent/WO1999002502A2/en not_active Ceased
- 1998-07-09 HU HU0003073A patent/HUP0003073A3/hu unknown
- 1998-07-09 BR BR9810991-0A patent/BR9810991A/pt not_active IP Right Cessation
- 1998-07-09 AU AU92578/98A patent/AU736256B2/en not_active Ceased
- 1998-07-09 DE DE69830405T patent/DE69830405T2/de not_active Expired - Fee Related
- 1998-07-09 AT AT98945162T patent/ATE296811T1/de not_active IP Right Cessation
- 1998-07-09 US US09/462,652 patent/US6316450B1/en not_active Expired - Fee Related
- 1998-07-09 KR KR1020007000201A patent/KR20010021643A/ko not_active Withdrawn
- 1998-07-09 CA CA002296033A patent/CA2296033A1/en not_active Abandoned
- 1998-07-10 TW TW087111166A patent/TW470743B/zh not_active IP Right Cessation
- 1998-07-10 AR ARP980103372A patent/AR013199A1/es not_active Application Discontinuation
-
2000
- 2000-01-10 NO NO20000108A patent/NO20000108L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW470743B (en) | 2002-01-01 |
| WO1999002502A2 (en) | 1999-01-21 |
| NZ501258A (en) | 2001-07-27 |
| NO20000108D0 (no) | 2000-01-10 |
| AU736256B2 (en) | 2001-07-26 |
| BR9810991A (pt) | 2000-08-08 |
| EP0994862B1 (de) | 2005-06-01 |
| TR200000073T2 (tr) | 2000-06-21 |
| EP0994862A2 (de) | 2000-04-26 |
| PL338016A1 (en) | 2000-09-25 |
| HUP0003073A2 (hu) | 2001-01-29 |
| ATE296811T1 (de) | 2005-06-15 |
| HUP0003073A3 (en) | 2002-10-28 |
| NO20000108L (no) | 2000-01-10 |
| DE69830405T2 (de) | 2006-01-26 |
| CA2296033A1 (en) | 1999-01-21 |
| AR013199A1 (es) | 2000-12-13 |
| WO1999002502A3 (en) | 1999-06-03 |
| JP2002511097A (ja) | 2002-04-09 |
| CN1261883A (zh) | 2000-08-02 |
| US6316450B1 (en) | 2001-11-13 |
| DE69830405D1 (de) | 2005-07-07 |
| KR20010021643A (ko) | 2001-03-15 |
| AU9257898A (en) | 1999-02-08 |
| IL133870A0 (en) | 2001-04-30 |
| CN1087294C (zh) | 2002-07-10 |
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